The newsletter · Sunday 20 September 2026

The Speedboat and the Sailboat

Omar Ladak holds six companies he never intends to sell. What he actually watches is on no dashboard, and he says so out loud.

Sent to subscribers on Substack and LinkedIn · Guest Omar Ladak

The episode behind thisEp 12: Automating Toward Freedom WatchYouTube: 32 minutes ReadFull transcript UseName the Human As sentSubstack As sentLinkedIn newsletter

One signal 📡 One subtractionOne analogy

Created by Sam Rogers of Snap Synapse | Episode 12 with guest Omar Ladak | The Sunday newsletter of the weekly show at sigsub.show

The test this week. For anything running in your name, name the accountable party, then name the backup. Where there's no second name, you own it, whether or not you meant to.


⛵ Analogy of the Week: The Speedboat and the Sailboat

A speedboat and a sailboat on open water, seen from behind, both heading away toward a distant headland. The speedboat trails a straight white wake. The sailboat, heeled on a tack, trails a sharp zigzag track across the same water

The speedboat is the mental model most of us carry to work. Point at the destination, fill the tank, go. Progress is the straight line, and anything else is a problem.

This week's guest, Omar Ladak, holds six construction and industrial services companies he never intends to sell. His correction isn't that we have no agency. He's explicit that we're not just leaves blowing in the wind. Three things are ours, but the fourth never will be.

  1. Where am I going?
  2. How effective is my vessel?
  3. How effective and whole is the crew?
  4. And then, in his words, "I must sail with whatever wind shows up." So...what now?

My own answer to the first one: helping people and machines work together so the decisions come out better and stay visible while it happens. The vessel and crew I can work on. The wind I can't. Such a good reminder!

Progress is measured against conditions, not the line we drew. Sometimes, when the wind is gone, "the most wise thing to do is literally just sit there and read a book."

He's candid that this doubles as an excuse generator if we let it, so he draws the line precisely:

The wind isn't the failure. Heading the wrong way regardless of the wind is.


📡 Signal: Neither countable nor showable

An exercise Omar runs on himself. Write down the ten most important things in your life and score each twice:

  1. how countable it is
  2. how visible it is to other people

The ones scoring high in both columns quietly get the energy, not because we decided they mattered most but because they're the ones we can point at. "We tend to wildly overindex the things we can count and show."

His own example is becoming a father: the most important relational thing he'd ever do, and doing it well meant lower scores everywhere else. Then the part that makes it a signal rather than a sentiment: "It really is invisible to everyone except for me, and hopefully one other person in the universe called my daughter."

Nothing in the reporting across his six companies would ever surface it. He watches it anyway.


➖ Subtraction: The name that isn't there

I ran my own inventory this week, across everything I've taken on in open source side projects. I expected to find things with no owner, the usual failure and easy to spot. Instead, every obligation named an accountable party and hardly any named a backup.

That's the distinction Omar makes by design and I'd never made at all: does this have to come back to me, or does an alternative exist? Regulation is no help here. It forces us to name accountability and never the second name.

Naming who's accountable tells you who to call. Naming the backup tells you what you actually own.

Omar's own cut is eleven years old and fits on a post-it: nothing further than six hours door to door from the office. It's cost them real deals, including a business he describes as beautiful. I don't have an equivalent yet.

You can now run the test on a page. Name the Human is a new agentic skill I'm sharing this week (also available as a structured prompt): a row for everything that acts without a human deciding first, ending in a named person or a visible blank. It fills the left of the table and refuses the right, because the empty cells are the finding: a register where every owner field says a squad name tells you nothing. New this week, every episode has one, all twelve at sigsub.show/takeaways. Tell me what you make of them, I'd love to hear about it!


▶️ Watch, read, or listen

![[newsletter/the-speedboat-and-the-sailboat/ep012_th.png]] Watch the full episode on YouTube, or find every format including the transcript at sigsub.show/episodes/ep-012. Also on Substack and LinkedIn.

Jump to a segment: what we can count and show · like being in a speedboat · just sit there and read a book · what am I automating towards · six hours door to door


🧭 Put It to Work

Six hundred people act on four questions clear enough that nothing routes back through him: why, who, where, and what now. He takes the second to the obvious place unprompted, which is not where most people go when defending a headcount. If the work is entirely AI generated, it may be just him and computers. "Okay, great, those are the who's."

I'd spent the same week asking one question of about fifty of my own repositories: is where this thing is going written down? Forty came back not to standard, including a security workflow from 2024 still running and never revised. The automation was fine. What it was automating toward was never expressed, which is the loss worth counting: not the thing that breaks loudly, but the thing that keeps running correctly toward something nobody chose.

So run the backup test on one thing this week. Then the choice this episode can help with. Where do you sit on the gradient from owner to operator, now that AI makes that placement a choice rather than a drift? Send me your answer, or bring it to the show.

Next week, the other half of a post-it rule: what makes a constraint simple enough that nobody has to ask you about it?

Godspeed,

Sam Rogers Trimming the Sail


Signals & Subtractions: what to watch, what to drop, every week

New here? Subscribe at sigsub.show and the next episode lands in your inbox.

This week's guest: Omar Ladak, co-founder of Noverra Group. As you heard on the episode, his inputs are intentionally limited, so mention the show if you want to connect.

Naming what an organization should do with AI, and what it should stop, is the work I do at Snap Synapse. If this issue described your week, say so and we'll talk it through. I'm also excited to be at Moonshots LIVE in LA this week! If you're going too, come find me.

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